TooMuchSiena Travel off the beaten path

Discover Montisi, off the beaten paths Valdorcia

Over the roofs of Montisi

When I think about a place for my retirement, I think at a place like Montisi, hidden gem between Valdorcia and Crete Senesi counting 400 residents.

A brief history

The foundation of Montisi dates back to Etruscan times to then become a fortified castle property of the family Cacciaconti degli Scialenga. The castle, strategically located on top of a hill near Trequanda, played an important role for Siena, and was heavily damaged and robbed after Siena’s decadence until it was included in the Grand Duchy of Tuscany i 1777.

Actually Montisi had also a Grancia, a fortified grange or manor, under the influence of Spedale di Santa Maria della Scala in Siena.  Built between 14th and 15th centuries, you can still see it at the end of the city center. Within the Grancia you can also admire the lovely Teatro della Grancia di Montisi, one of the smallest theaters in Italy with only 52 seats, re-opened in 200o and run by the Dutch Cristine. In May there is also the Montisi Italian Film Festival, with lots of screenings of contemporary artists as well as great Italian directors.

Corner of Montisi

Corner of Montisi

View from Montisi - Valdorcia

View from Montisi – Valdorcia

On top of the hamlet you can still recognize the cassero architecture, as well as have a breathtaking view over Valdorcia from the ancient gates. The narrow streets are lovely and full of colorful flowers and doors. One of those streets has a funny name, since it’s called “Via del culo” (Bottom’s street), probably because of its narrow shape. The atmosphere is peaceful and charming, as you will see from the happy faces of people living there.

People from Montisi

Vitis Vinifera - wine bar in Montisi

Vitis Vinifera – wine bar in Montisi

As I’ve just said people from Montisi looks really happy and smiling. There are about 400 people living there and some of them are foreign people felt in love with this charming hamlet several years ago. Among them there is Antonella, a strong Sardinian woman, who runs the Vitis Vinifera together with her partner and famous oenologist Maurizio Castelli. This is a wine bar and shop where you can really learn how to
taste wine, as well as learn more about Italian food culture. In addition Antonella is a certified ONAF cheese taster and she definitively knows how to put together wine and cheese as the perfect match.

Another “straniero” or foreigner as locals call who was not born here, who chose Montisi as his buen retiro is Francesco. He escaped from the crowded Milan in the 80s and decide to open Officina Sospesa, his magic workshop where he realizes great puppets. Francesco is indeed a famous puppeteer, one of the few left in Italy, who still creates its wooden friends with passion and love. But Francesco also free his puppets from strings by transforming them into symbolic and colorful sculptures.

Then walking around you can meet Marisa, a lovely nonna, nicknamed the Beast. She roars but she would definitely smile and say hi to you, as well as telling the latests gossips in town. You can meet Carlotta the pig and lots of sleepy cats around, together with lots of nice faces.

Francesco, the puppeteer

Francesco, the puppeteer

People from Montisi are strongly related to their contrada. As a matter of fact the town has four city quarters, San Martino, Torre, Piazza and Castello, that will fight each other during the Giostra del Simone. The Jouster, held every year on the first weekend of August, took its name from Simone Caccianti, who owned and controlled Montisi at the end of 13th century. He robbed and mistreated the town and its inhabitants, so when he was killed Montisi people decided to name the jouster’s puppet after him.

Dolce vita in Montisi

Dolce vita in Montisi


  • Visit the belvedere on the back of the S.S. Annunziata Church. From there you can have great views over Valdorcia and Montisi hamlet
  • Walk around slowly and enjoy the dolce vita of Montisi. Say Ciao to Marisa, while you walk around!
  • Have a glass of wine with Antonella, she’ll teach how to really enjoy wine and cheese!
  • Come for the Olive Oil Festival during the first weekend of November. Montisi is indeed very renowned for its extra virgin olive oil. Even Gerard Depardieu comes every here to but oil for its restaurants!

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